Benzyl 4-[3-(3-nitrobenzyl)indol-1-yl]-4-oxobutyrate → 4-[3-(3-Aminobenzyl)indol-1-yl]-4-oxobutyric acid

HRID 249158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249158
[N+:1]([C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][CH:33]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17](=[O:30])[CH2:18][CH2:19][C:20]([O:22]CC2C=CC=CC=2)=[O:21])[CH:9]=1)([O-])=O>O1CCOCC1.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][CH:33]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17](=[O:30])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:9]=1

Komponenten

5

Edukt 1

HCID 19024729Benzyl 4-[3-(3-nitrobenzyl)indol-1-yl]-4-oxobutyrate

Produkt 1

HCID 190246994-[3-(3-Aminobenzyl)indol-1-yl]-4-oxobutyric acidAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of benzyl 4-[3-(3-nitrobenzyl)indol-1-yl]-4-oxobutyrate (320 mg) in a mixture of 1,4-dioxane (6 ml) and methanol (3 ml) was added 10% palladium on activated carbon (60 mg), and the mixture was shaken under hydrogen atmosphere (3 atm) at 25° C. for 1.5 hours. The catalyst was filtered off and the filtrate was evaporated. The crude crystals were washed with hot chloroform and hot ethyl acetate to give 4-[3-(3-aminobenzyl)indol-1-yl]-4-oxobutyric acid (157 mg).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. washThe crude crystals were washed with hot chloroform and hot ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f3c4615afbf745679a7cd2275ebec788
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212320

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